Pyrrolidine → HCID 68665582, compound

Participants

Reaction Steps

A mixture of pyrrolidine (0.032 g, 0.46 mmol) and 1-[4-(4-chloromethyl-oxazol-2-yl)-benzyl]-1H-benzoimidazole (0.05 g, 0.15 mmol) in a sealed tube at room temperature was stirred for 30 minutes. The tube was unsealed and the reaction mixture was concentrated in vacuo to remove the excess pyrrolidine. The residue was purified by column chromatography (silica, CHCl3/CH3OH 4%). The purified free base was treated with methanolic HCl solution, stirred for several minutes at room temperature and evaporated to dryness to afford the title product as a white solid in 51% yield, identified by NMR and mass spectral analyses. 1H NMR (300 MHz, DMSO-d6): 9.35 (s, 1H); 8.33 (s, 1H); 8.00 (d, 2H); 7.85 (m, 1H); 7.74 (m, 1H); 7.59 (d, 2H); 7.49 (m, 2H); 5.79 (s, 2H); 4.35 (s, 2H); 3.36 (m br, 4H); 1.98 (m, 4H)). LCMS (ESI+) 359 (MH+).

Provenance & Evidence